2,5-Dimethylbufotenine and 2,5-dimethylbufotenidine: Novel derivatives of natural tryptamines found in Bufo alvarius toads

Abstract

The solid-state structure of the bufotenine derivative bis(5-methoxy-2,N,N-trimethyltryptammonium) (5-MeO-2-Me-DMT) fumarate (systematic name: bis{[2-(5-methoxy-2-methyl-1H-indol-3-yl)ethyl]dimethylazanium} (2E)-but-2-enedioate), 2C14H21N2O+·C4H2O4 2-, the bufotenidine derivative 5-methoxy-2,N,N,N-tetramethyltryptammonium (5-MeO-2-Me-TMT) iodide {systematic name: [2-(5-methoxy-2-methyl-1H-indol-3-yl)ethyl]trimethylazanium iodide}, C15H23N2O+·I-, and the hydrate of the same {systematic name: [2-(5-methoxy-2-methyl-1H-indol-3-yl)ethyl]trimethylazanium iodide monohydrate}, C15H23N2O+·I-·H2O, are reported. The structure of 5-MeO-2-Me-DMT fumarate possesses one tryptammonium cation and a half of a fumarate dianion in the asymmetric unit, linked together by N - H⋯O hydrogen bonds in infinite two-dimensional networks parallel to the (101) plane. The structure of 5-MeO-2-Me-TMT iodide possesses one tryptammonium cation and one iodide anion in the asymmetric unit. The ions are linked via N - H⋯I hydrogen bonds, and indoles are coupled in dimers through π-π interactions. The hydrate of 5-MeO-2-Me-TMT iodide possesses one tryptammonium cation, one iodide anion and one water molecule in the asymmetric unit. It shows N - H⋯I and O - H⋯I hydrogen bonds that couple the tryptammonium cations into dimers.